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Chicago Marathon Race Guide + Tips

Every October, thousands of runners flock to the Midwest for the Bank of America Chicago Marathon. They’ll wind through the city’s diverse neighborhoods and enjoy a famously flat course. After 26.2 miles, they’ll drink a 312 and proudly wear their finish medal around town (maybe to Giordano’s for thin crust pizza if they know what’s …

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Ultimate Guide to Taking a Baby to a Cubs Game at Wrigley Field

There is something magical about watching the Chicago Cubs play baseball at Wrigley Field. The ivy-covered outfield walls and manual scoreboard are as iconic as the Chicago-style hot dog itself — which is required eating in the Friendly Confines. It’s no surprise that a parent would want to bring their baby to a Chicago Cubs …

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12-Day Road Trip from Orlando to Chicago via Washington, DC

We had a doctors appointment in Chicago and currently live in Orlando. Instead of flying in for a quick trip, we decided to pack up the car and our toddler for a 12-day cross-country adventure. In this trip report, we’re sharing everywhere we went and everything we did in our journey across the country. Deciding …

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Christmas in Chicago Planning Guide — Best things to do + Sample Itinerary

Maybe it’s because I grew up in a small town, but I’ve romanticized Christmas in a big city. There’s something about the twinkle of skyscrapers in the early evening and the sidewalks bustling as the shoppers rush home with their treasures, if you will. Christmas in any city seems magical, but Christmas in Chicago specifically …

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